CAS 68-12-2|dimethylformamide|N,N-dimethylformamide|Dimethylformamide|<i>N</i>,<i>N</i>-Dimethylmethanamide|N,N-DIMETHYLFORMAMIDE ACS REAGENT GRADE|DMF|N-Formyldimethylamine|NCI-c60913|N,N-Dimethylf...

General Information

Structure

Molecular Formula

C₃H₇NO

Molecular Mass

73.09378

Exact Mass

73.05276385

Charge

InChI

InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3

InChIKey

ZMXDDKWLCZADIW-UHFFFAOYSA-N

Canonic Smiles

O=CN(C)C

Isomeric Smiles

CN(C)C=O

Calculated Properties

JChem

LogD (pH = 7.4)

-0.63

LogD (pH = 5.5)

-0.63

Log P

-0.63

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

-1.26

Polar Surface Area

20.31

Polarizability

7.67

Molar Refractivity

19.77

LOG S

0.74

Data Source

Academic Data

Data Source

Names and Identifiers

IUPAC name

N,N-dimethylformamide

Synonyms

DimethylformamideN,N-DimethylmethanamideNCI-c60913N,N-DIMETHYLFORMAMIDE ACS REAGENT GRADEN-FormyldimethylamineDMFN,N-Dimethylformamide 99.8%N,N-DIMETHYLFORMAMIDEN,N-DIMETHYL FORMAMIDEN,N-DIMETHYLFORMAMIDE, BIO GRADEN,N-DIMETHYLFORMAMIDE, ANHYDROSOLV GRADEN,N-二甲基甲酰胺N,N-DimethylformamideN,N-DIMETHYLFORMAMIDE, HPLC/SPECTRO GRADEN,N-Dimethylformamide, anhydrous, amine freeN,N-二甲基甲酰胺, HPLC 级N,N-Dimethylformamide, HPLC GradeN,N-二甲基甲酰胺, 无水N,N-二甲基甲酰胺, 无水, 无氨N,N-Dimethylformamide, anhydrousN,N-二甲基甲酰胺, HPLC级N,N-二甲基甲酰胺, 光谱级N,N-Dimethylformamide, Spectrophotometric GradeN,N-二甲基甲酰胺, ACSN,N-Dimethylformamide, ACSN,N-dimethylformamideN-FormyldimethylamineN,N-DimethylmethanamideN,N-DimethylformamideN,N-dimethylformamideDMFDimethylformamide

IUPAC Traditional name

dimethylformamide

Names and Identifiers

Registration numbers

MDL Number

Merck Index

Beilstein Number

EC Number

PubChem SID

248650912486508624849479248563792487290724883591248679122485920024849438248599401609650712488640124867382248784022489388324853607465060368144024

CAS Number

68-12-2

PubChem CID

6228

KEGG ID

C03134

Unique Ingredient Identifier

CHEMBL

Wikipedia Title

DrugBank ID

Chemspider ID

MeSH Name

CHEBI ID

17741CHEBI:12425CHEBI:7076CHEBI:21454CHEBI:17741CHEBI:42077

BRENDA Database

4.1.2.133.1.1.742.4.1.2452.3.2.133.2.1.14.6.1.133.5.1.561.17.3.21.10.3.22.4.1.905.4.99.71.1.1.1493.5.1.113.3.2.10

Protein Data Bank

6hsh4p0h6d5o4j656hu34cqf6gxw1thn4abj7est5fue6a7b3rcg6wnk6hu16est

Patent number

WO2006008751US2007219384US2006122226US2004162341US2005101631WO2008119015WO2006026368EP1619191US2006199820US2007043035US2008249128US2006199242US2008268044WO2006073518

UniProt Database

Q93MW7Q9LCC1Q9ER35Q9LCC0Q5U780Q9H479Q9Y948C9DQ22C9DQ21

MetaboLights Database

MTBLS2967MTBLS615MTBLS808MTBLS392MTBLS3322MTBLS601MTBLS2824MTBLS606MTBLS1115MTBLS3854

NMRShiftDB Database

10009017

EnzymePortal Database

C9DQ21Q9LCC1C9DQ22Q9LCC0

PubMed Citation Links

3824392186661981960821523313473

ACToR Database

114057-15-768-12-2

Reaxys Registry

605365

BRENDA Ligand Database

BKMS React Database

CompTox Database

SureChEMBL Database

HMDB Database

Rhea Database

PDBeChem Database

IntEnz Database

MetaCyc Database

ArrayExpress (Gene Expression Altlas)

E-GEOD-11758

Registration numbers

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB01844

Drug Groups

experimental

References

• Redlich CA, Beckett WS, Sparer J, Barwick KW, Riely CA, Miller H, Sigal SL, Shalat SL, Cullen MR: Liver disease associated with occupational exposure to the solvent dimethylformamide. Ann Intern Med. 1988 May;108(5):680-6. [Pubmed]

External Links

• [Wikipedia]

Apollo Scientific

OR16840

For Peptide Synthesis

MP Biomedicals

02191417

ACS Reagent Grade
Specific Gravity: 0.944 g/ml
b.p. 152-154°C
Clear, liquid

02194818

Molecular Biology Reagent
Purity: 99+%
A solvent for chromogenic substrates in molecular biology experiments.

1 ml = ~0.94 g

D8300

Application
多种疏水性有机化合物的溶剂。

D4551

Application
多种疏水性有机化合物的溶剂。
包装
250, 500 mL in glass bottle

539465

Application
Solvent for many hydrophobic organic compounds.
Legal Information
AldraSORB is a trademark of Sigma-Aldrich Co. LLC

40250

Application
Solvent for many hydrophobic organic compounds.
Other Notes
Sales restrictions may apply

40243

Application
Solvent for many hydrophobic organic compounds.
General description
no impurities present which would show greater signals than 5 ng/l lindane, in the GC/ECD retention time range of lindane to DDT

40249

Application
Solvent for many hydrophobic organic compounds.
Other Notes
Sales restrictions may apply
Packaging
tri Q-Multi-way barrel (further details see appendix)

40246

Application
Solvent for many hydrophobic organic compounds.
General description
Special brochure (85475) available at cost price.
Other Notes
Sales restrictions may apply

ChEBI

CHEBI:17741

A member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.

Molecule Details

References

PubChem Literature

From Data Sources

• In combination with POCl₃, (COCl)₂, etc., generates an iminium chloride intermediate for the formylation of reactive aromatic nuclei by the Vilsmeier reaction:

• DMF can also be used for formylation with alkyllithium or Grignard reagents: Synthesis, 228 (1984).

• Dipolar aprotic solvent, in which anions have enhanced nucleophilicity, compare Dimethyl sulfoxide, A13280. Effective solvent for a vast range of reactions.

• Compare also N-Methylformanilide, A11829, and preformed Vilsmeier reagent (Chloromethylene)dimethylammonium chloride, B24172. Monograph: Synthesis Using Vilsmeier Reagents, C. M. Marson, P. R. Giles, CRC Press, Boca Raton, FL (1994). Formylation can be extended to less active substrates, e.g. acenaphthene or mesitylene, with the DMF-triflic anhydride reagent: J. Chem. Soc., Chem. Commun., 1571 (1990). Under Vilsmeier conditions, electron-rich alkenes can be converted to ɑ?-unsaturated aldehydes; see, e.g.: Synthesis, 752 (1976); and ketones to ?-chloroenals: Synthesis, 496 (1985); Org. Synth. Coll., 5, 215 (1973).

• Vilsmeier conditions also promote dehydrations, e.g. in cyclodehydration of hydroxyphenols to give cyclic ethers, as an efficient alternative to the Mitsunobu reaction: J. Chem. Soc., Perkin 1, 2249 (1996); J. Org. Chem., 59, 4346 (1994):

• In aqueous DMF, tosylate esters undergo formolysis to formate esters: Synth. Commun., 26, 1031 (1996).

• CAUTION! Thermal runaway reactions can occur with NaH; see Sodium hydride, 13431.

• For the free-radical formylation of perfluoroalkyl iodides, see Zinc-copper couple, L09811.

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

Data Source

• Academic Data

• Commercial Catalog

Names and Identifiers

• IUPAC name

• Synonyms

• IUPAC Traditional name

Registration numbers

• MDL Number

• Merck Index

• Beilstein Number

• EC Number

• PubChem SID

• CAS Number

• PubChem CID

• KEGG ID

• Unique Ingredient Identifier

• CHEMBL

• Wikipedia Title

• DrugBank ID

• Chemspider ID

• MeSH Name

• CHEBI ID

• BRENDA Database

• Protein Data Bank

• Patent number

• UniProt Database

• MetaboLights Database

• NMRShiftDB Database

• EnzymePortal Database

• PubMed Citation Links

• ACToR Database

• Reaxys Registry

• BRENDA Ligand Database

• BKMS React Database

• CompTox Database

• SureChEMBL Database

• HMDB Database

• Rhea Database

• PDBeChem Database

• PDB Bank

• DrugBank

• Apollo Scientific

• MP Biomedicals

• Wikipedia

• Sigma Aldrich

• ChEBI

Molecule Details

References

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

IUPAC name

N,N-dimethylformamide

Synonyms

IUPAC Traditional name

dimethylformamide

From Data Sources

• In combination with POCl₃, (COCl)₂, etc., generates an iminium chloride intermediate for the formylation of reactive aromatic nuclei by the Vilsmeier reaction:

• DMF can also be used for formylation with alkyllithium or Grignard reagents: Synthesis, 228 (1984).

• Dipolar aprotic solvent, in which anions have enhanced nucleophilicity, compare Dimethyl sulfoxide, A13280. Effective solvent for a vast range of reactions.

• In aqueous DMF, tosylate esters undergo formolysis to formate esters: Synth. Commun., 26, 1031 (1996).

• CAUTION! Thermal runaway reactions can occur with NaH; see Sodium hydride, 13431.

• For the free-radical formylation of perfluoroalkyl iodides, see Zinc-copper couple, L09811.

MDL Number

MFCD00003284

Beilstein Number

605365

Unique Ingredient Identifier

8696NH0Y2X

Wikipedia Title

Dimethylformamide

NMRShiftDB Database

10009017

EnzymePortal Database

C9DQ21Q9LCC1C9DQ22Q9LCC0

PubMed Citation Links

3824392186661981960821523313473

ACToR Database

114057-15-768-12-2

Reaxys Registry

605365

BRENDA Ligand Database

BKMS React Database

CompTox Database

SureChEMBL Database

HMDB Database

Rhea Database

PDBeChem Database

IntEnz Database

MetaCyc Database

ArrayExpress (Gene Expression Altlas)

E-GEOD-11758

DrugBank

DB01844

Drug Groups

experimental

References

External Links

• [Wikipedia]

Apollo Scientific

OR16840

For Peptide Synthesis

MP Biomedicals

02191417

ACS Reagent Grade
Specific Gravity: 0.944 g/ml
b.p. 152-154°C
Clear, liquid

02194818

Molecular Biology Reagent
Purity: 99+%
A solvent for chromogenic substrates in molecular biology experiments.

02195147

1 ml = ~0.94 g

Sigma Aldrich

D8300

Application
多种疏水性有机化合物的溶剂。

D4551

Application
多种疏水性有机化合物的溶剂。
包装
250, 500 mL in glass bottle

539465

Application
Solvent for many hydrophobic organic compounds.
Legal Information
AldraSORB is a trademark of Sigma-Aldrich Co. LLC

40250

Application
Solvent for many hydrophobic organic compounds.
Other Notes
Sales restrictions may apply

40243

40249

Application
Solvent for many hydrophobic organic compounds.
Other Notes
Sales restrictions may apply
Packaging
tri Q-Multi-way barrel (further details see appendix)

40246

Application
Solvent for many hydrophobic organic compounds.
General description
Special brochure (85475) available at cost price.
Other Notes
Sales restrictions may apply

ChEBI

CHEBI:17741

A member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.

Physical Property

Safety Information

Flammable/Harmful/Irritant/Teratogenic/Store under Argon

Hygroscopic

S:16-45-53

Product Information

λ: 295 nm Amax: 0.10

λ: 290 nm Amax: 0.14

λ: 340-400 nm Amax: 0.01

Storage Condition

Room Temperature (15-30°C), Avoid excess heat

Room Temperature (15-30°C)

Hazard Class

Emergency Response Guidebook(ERG) Number

129

RTECS

LQ2100000

European Hazard Symbols

Toxic (T)

Flammable (F)

Risk Statements

R:10-20/21-36-61

r61,r20/21,r36

61-20/21-36

EU Hazard Identification Number

UN Number

2265

UN2265

Packing Group

III

EU Classification

LD50

1.5 g kg^-1 (dermal, rabbit)

2.8 g kg^-1 (oral, rat)

GHS Signal Word

DANGER

Danger

GHS Pictograms

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Flammable gases, category 1

Flammable aerosols, categories 1,2

Flammable liquids, categories 1,2,3

Self-reactive substances and mixtures, Types B,C,D,E,F

Pyrophoric liquids, category 1

Pyrophoric solids, category 1

Self-heating substances and mixtures

Substances and mixtures, which in contact with water, emit flammable gases, categories 1,2,3

Organic peroxides, Types B,C,D,E,F

Respiratory sensitization, category 1

Germ cell mutagenicity, categories 1A,1B,2

Carcinogenicity, categories 1A,1B,2

Reproductive toxicity, categories 1A,1B,2

Specific Target Organ Toxicity – Single exposure, categories 1,2

Specific Target Organ Toxicity – Repeated exposure, categories 1,2

Aspiration Hazard, category 1

Respiratory sensitization, category 1

Germ cell mutagenicity, categories 1A,1B,2

Carcinogenicity, categories 1A,1B,2

Reproductive toxicity, categories 1A,1B,2

Specific Target Organ Toxicity – Single exposure, categories 1,2

Specific Target Organ Toxicity – Repeated exposure, categories 1,2

Aspiration Hazard, category 1

Flammable gases, category 1

Flammable aerosols, categories 1,2

Flammable liquids, categories 1,2,3

Self-reactive substances and mixtures, Types B,C,D,E,F

Pyrophoric liquids, category 1

Pyrophoric solids, category 1

Self-heating substances and mixtures

Substances and mixtures, which in contact with water, emit flammable gases, categories 1,2,3

Organic peroxides, Types B,C,D,E,F

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Explode Limits

2.2–15.2%

15.2 %

NFPA704

EU Index

616-001-00-X

GHS Hazard statements

226,312,319,332,360

H226-H312-H319-H332-H360D

H226-H312+H332-H319-H360D

H360-H226-H312-H332-H319

GHS Precautionary statements

280,305+351+338,308+313

P201-P280-P305+P351+P338-P308+P313

P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A

Personal Protective Equipment

Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

German water hazard class

RID/ADR

UN 2265 3/PG 3

TSCA Listed

是

Grade

Purity

Suitability

suitable for neutral marker for measuring electroosmotic flow (EOF)

suitable for solvent for chromogenic substrates (X-Gal, etc.) used in molecular biology applications.

GC-Headspace tested

passes test for IR spectroscopy

passes test for suitability for UV spectroscopy

Evaporation Residue

<0.0005%

≤0.005%

≤0.0005%

Linear Formula

HCON(CH3)2

Impurities

Cation Traces

1 cm path, H2O reference

H2O reference

Shelf Life

(limited shelf life, expiry date on the label)

Quality

for pesticide residue analysis

over molecular sieve (H2O ≤0.01%)

over molecular sieve (H2O ≤0.005%)

abs.

Purified By

glass distillation

Appearance

APHA: ≤15

Packaging

ampule of 1000 mg

packaged under Argon in resealable ChemSeal? bottles

Molecule

ID:1614