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123-39-7

Basic Information
CAS No.: 123-39-7
Name: N-Methylformamide
Article Data: 59
Cas Database
Molecular Structure:
Molecular Structure of 123-39-7 (N-Methylformamide)
Formula: C2H5NO
Molecular Weight: 59.0678
Synonyms: Methylformamide;Monomethylformamide;N-Methylformimidic acid;N-Monomethylformamide;NSC 3051;Formamide, N-methyl-;Formamide, N-methyl- (8CI 9CI);methanimidic acid, methyl-;
EINECS: 204-624-6
Density: 0.872 g/cm3
Melting Point: -3.2 °C
Boiling Point: 182.5 °C at 760 mmHg
Flash Point: 81.5 °C
Solubility: infinitely soluble in water
Appearance: clear colourless liquid
Hazard Symbols: ToxicT
Risk Codes: 61-21
Safety: 53-45
Transport Information: N/A
PSA: 29.10000
LogP: 0.38900
Synthetic route
3294-31-3

triethyl(methylamino)silane

18243-21-5

trimethylsilyl formate

A

123-39-7

N-Methylformamide

B

107-46-0

Hexamethyldisiloxane

C

2652-41-7

1,1,1-triethyl-3,3,3-trimethyl-disiloxane

D

994-49-0

hexaethyl disiloxane

Conditions
ConditionsYield
for 1h; Ambient temperature;A 100%
B 21.5%
C 23.6%
D 44.5%
at 20℃; for 1h; Product distribution; Mechanism; various amides as catalysts;A 100%
B 21.5%
C 23.6%
D 44.5%
at 20℃; for 1h;A 100%
B 21.5%
C 23.6%
D 44.5%
3294-31-3

triethyl(methylamino)silane

A

123-39-7

N-Methylformamide

B

107-46-0

Hexamethyldisiloxane

C

2652-41-7

1,1,1-triethyl-3,3,3-trimethyl-disiloxane

D

994-49-0

hexaethyl disiloxane

Conditions
ConditionsYield
With trimethylsilyl formate at 20℃; for 1h;A 100%
B 21.5%
C 23.6%
D 44.5%
107-31-3

Methyl formate

593-51-1

methylamine hydrochloride

123-39-7

N-Methylformamide

Conditions
ConditionsYield
With sodium methylate In methanol Ambient temperature;99%
64-18-6

formic acid

74-89-5

methylamine

123-39-7

N-Methylformamide

Conditions
ConditionsYield
With aluminum oxide at 40℃; for 0.166667h; Neat (no solvent); Cooling with ice;98%
107-31-3

Methyl formate

74-89-5

methylamine

123-39-7

N-Methylformamide

Conditions
ConditionsYield
at 40 - 50℃;93.5%
In water at 25℃; for 1h;82%
With methanol
at 40 - 130℃;
18952-41-5

N-methylmethanethioamide

123-39-7

N-Methylformamide

Conditions
ConditionsYield
With tetrabutylammonium periodite In dichloromethane at 20℃; for 0.75h;86%
93214-66-5

α-(4-tert-Butoxy-2,6-di-tert-butyl-1-oxo-2,5-cyclohexadienyl)-N-tert-butylnitron

A

123-39-7

N-Methylformamide

B

2425-74-3

t-butylformamide

C

27701-01-5

methyl N-tert-butylcarbamate

D

7330-85-0

4-tert-Butoxy-2,6-di-tert-butylphenol

Conditions
ConditionsYield
With hydrogenchloride In methanol for 8h; Ambient temperature;A n/a
B n/a
C n/a
D 85%

[((η5-C5H3)2(SiMe2)2)Ru2(μ-H)(CO)4]BF4

74-89-5

methylamine

A

123-39-7

N-Methylformamide

B

287097-09-0

[(η5-C5H3)2(Si(CH3)2)2]Ru2(CO)4

C

287097-18-1

((η5-C5H3)2(SiMe2)2)Ru2(CO)3(NH2Me)

Conditions
ConditionsYield
With triphenylmethane In benzene-d6 amine was bubbled through a soln. in C6D6 in NMR tube for 5 min (Ar); not sepd., detected by NMR spectra;A 84%
B 5%
C n/a
18243-21-5

trimethylsilyl formate

A

123-39-7

N-Methylformamide

B

107-46-0

Hexamethyldisiloxane

C

2652-41-7

1,1,1-triethyl-3,3,3-trimethyl-disiloxane

D

994-49-0

hexaethyl disiloxane

Conditions
ConditionsYield
With N-Methylformamide; triethyl(methylamino)silane at 20℃; for 0.0333333h;A 80.2%
B 45.2%
C 13.1%
D 41.5%
10352-28-0

N-(2-benzoyl-4-chlorophenyl)formamide

74-88-4

methyl iodide

A

123-39-7

N-Methylformamide

B

52395-00-3

N-methyl-N-(2-benzoyl-4-chlorophenyl)formamide

Conditions
ConditionsYield
In N-methyl-acetamide; water; mineral oilA n/a
B 70%
In N-methyl-acetamide; water; mineral oilA n/a
B 70%
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Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Specification

1. Introduction of N-methylformamide
The N-methylformamide, with the CAS registry number 123-39-7, is also called Monomethylformamide. It is a kind of clear colourless liquid, and infinitely soluble in water.

2. Properties of N-methylformamide
(1)ACD/LogP: -0.60; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.6; (4)ACD/LogD (pH 7.4): -0.6; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 11.27; (8)ACD/KOC (pH 7.4): 11.27; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 20.31 Å2; (13)Index of Refraction: 1.364; (14)Molar Refractivity: 15.09 cm3; (15)Molar Volume: 67.6 cm3; (16)Polarizability: 5.98×10-24cm3; (17)Surface Tension: 23.2 dyne/cm; (18)Density: 0.872 g/cm3; (19)Flash Point: 81.5 °C; (20)Enthalpy of Vaporization: 41.87 kJ/mol; (21)Boiling Point: 182.5 °C at 760 mmHg; (22)Vapour Pressure: 0.808 mmHg at 25°C.

3. Structure Descriptors of N-methylformamide
(1)SMILES: O=CNC
(2)InChI: InChI=1/C2H5NO/c1-3-2-4/h2H,1H3,(H,3,4)
(3)InChIKey: ATHHXGZTWNVVOU-UHFFFAOYAO

4. Toxicity of N-methylformamide

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD intravenous > 568mg/kg (568mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL) National Technical Information Service. Vol. PB82-232158,
guinea pig LD50 unreported 465mg/kg (465mg/kg) SENSE ORGANS AND SPECIAL SENSES: CORNEAL DAMAGE: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

MUSCULOSKELETAL: OTHER CHANGES
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 57(2), Pg. 30, 1992.
mouse LD50 intramuscular 2700mg/kg (2700mg/kg)   Toxicology. Vol. 34, Pg. 173, 1985.
mouse LD50 intraperitoneal 802mg/kg (802mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 intravenous 1580mg/kg (1580mg/kg)   Toxicology. Vol. 34, Pg. 173, 1985.
mouse LD50 oral 2600mg/kg (2600mg/kg)   Toxicology. Vol. 34, Pg. 173, 1985.
mouse LD50 subcutaneous 3100mg/kg (3100mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION Dissertation Abstracts International, B: The Sciences and Engineering. Vol. 40, Pg. 549, 1979.
mouse LD50 unreported 1175mg/kg (1175mg/kg) SENSE ORGANS AND SPECIAL SENSES: CORNEAL DAMAGE: EYE

MUSCULOSKELETAL: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 57(2), Pg. 30, 1992.
rat LD50 intraperitoneal 3500mg/kg (3500mg/kg)   Journal of Reproduction and Fertility. Vol. 4, Pg. 219, 1962.
rat LD50 oral 4gm/kg (4000mg/kg)   Journal of Reproduction and Fertility. Vol. 4, Pg. 219, 1962.
rat LD50 subcutaneous > 2500mg/kg (2500mg/kg)   Naunyn-Schmiedebergs Archiv fuer Pharmakologie und Experimentelle Pathologie. Vol. 257, Pg. 296, 1967.
rat LD50 unreported 2400mg/kg (2400mg/kg) SENSE ORGANS AND SPECIAL SENSES: CORNEAL DAMAGE: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

MUSCULOSKELETAL: OTHER CHANGES
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 57(2), Pg. 30, 1992.

5. Safety Information of N-methylformamide
Hazard Symbols:ToxicT
Risk Codes:
R61:May cause harm to the unborn child. 
R21:Harmful in contact with skin.
Safety Description:
S53:Avoid exposure - obtain special instructions before use. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

6. Preparation of N-methylformamide
N-methylformamide is prepared by methylamine and methyl formate:
CH3NH2 + HCOOCH3 → CH3NHCHO + CH3OH

7. Use of N-methylformamide
N-methylformamide is used as a precursor to methyl isocyanide, a ligand in coordination chemistry and an intermediate in the production of some pharmaceutical compounds. It is also mainly used as a reagent in various organic syntheses with limited applications as a highly polar solvent.

8. Other details of N-methylformamide
You should be cautious while dealing with N-methylformamide. Itis harmful in contact with skin, and may cause harm to the unborn child. Therefore, you had better take the following instructions: Avoid exposure - obtain special instruction before use, and In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)

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