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Hexamethyleneimine

CAS No.
111-49-9
Chemical Name:
Hexamethyleneimine
Synonyms
Azepan;HMI;AZACYCLOHEPTANE;g0;0402;PERHYDROAZEPINE;HEXAHYDROAZEPINE;HEXAMETHYLENIMINE;1-Azacycloheptane;G 0
CBNumber:
CB6852841
Molecular Formula:
C6H13N
Molecular Weight:
99.17
MDL Number:
MFCD00006934
MOL File:
111-49-9.mol
MSDS File:
SDS
Last updated:2023-10-22 18:52:18

Hexamethyleneimine Properties

Melting point -37°C
Boiling point 138 °C749 mm Hg(lit.)
Density 0.88 g/mL at 25 °C(lit.)
vapor pressure 7.4 mm Hg ( 21.1 °C)
refractive index n20/D 1.466(lit.)
Flash point 65 °F
storage temp. Poison room
form Liquid
pka pK1:11.07 (25°C)
color Clear colorless to light yellow
Odor Ammonia-like.
explosive limit 1.6-9.9%(V)
Water Solubility soluble
BRN 1084
LogP 1.7
CAS DataBase Reference 111-49-9(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII CZD076G73R
NIST Chemistry Reference 1H-Azepine, hexahydro-(111-49-9)
EPA Substance Registry System 1H-Azepine, hexahydro- (111-49-9)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS02,GHS05,GHS06
Signal word  Danger
Hazard statements  H225-H300-H314-H331
Precautionary statements  P210-P261-P264-P280-P301+P310-P305+P351+P338
Hazard Codes  T,T+,F
Risk Statements  10-20-25-34-28-11
Safety Statements  26-36/37/39-45-28A-16-1
RIDADR  UN 2493 3/PG 2
WGK Germany  3
RTECS  CM3150000
Autoignition Temperature 255 °C
TSCA  Yes
HS Code  2933 99 80
HazardClass  3
PackingGroup  II
Toxicity LD50 orally in Rabbit: 410 mg/kg
NFPA 704
3
4 0

Hexamethyleneimine price More Price(15)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich H10401 Hexamethyleneimine 99% 111-49-9 25ml $33 2023-06-20 Buy
Sigma-Aldrich H10401 Hexamethyleneimine 99% 111-49-9 100ml $47.4 2023-06-20 Buy
TCI Chemical H0092 Hexamethyleneimine 111-49-9 25ML $16 2023-06-20 Buy
TCI Chemical H0092 Hexamethyleneimine 111-49-9 500ML $42 2023-06-20 Buy
Alfa Aesar B24007 Hexamethyleneimine, 98+% 111-49-9 100ml $26.1 2023-06-20 Buy
Product number Packaging Price Buy
H10401 25ml $33 Buy
H10401 100ml $47.4 Buy
H0092 25ML $16 Buy
H0092 500ML $42 Buy
B24007 100ml $26.1 Buy

Hexamethyleneimine Chemical Properties,Uses,Production

Chemical Properties

clear colorless to light yellow liquid

Uses

Hexamethyleneimine is used as a pharmaceutical product and raw material for rubber products. It is also used as a intermediate for agrochemicals, zeolites, dyes , inks, rubber chemicals, textile chemicals, corrosion inhibitors, ore flotation.

Uses

A degradation product of herbicide Molinate in pot soil and rice plants.

Production Methods

Hexamethyleneimine is produced in 84% yield by heating hexamethylenediamine at 350 ℃ in a stream of hydrogen. The catalyst, ammonium vanadate on activated alumina, is prereduced with hydrogen at 500 ℃. Residues from the industrial distillation of hexamethylenediamine can be converted into hexamethyleneimine over aluminum silicate or aluminum oxide in a stream of nitrogen. For the preparation from caprolactam]. Hexamethyleneimine can be prepared by dimerizing acrolein, reducing the product to 2- hydroxymethyltetrahydropyran, expanding the ring to give oxepane, followed by treatment with ammonia over aluminum oxide at 350 ℃.

Application

The most important use is the conversion of hexamethyleneimine into S-ethylhexahy- dro-1H-azepine-1-carbothioate, the selective rice herbicide Molinate (C2H5 S–CO–NC6H12 , Zeneca).

Definition

ChEBI: An azacycloalkane that is cycloheptane in which one of the carbon atoms is replaced by a nitrogen atom.

General Description

A colorless liquid with an ammonia-like odor. Flash point 65°F. Toxic by ingestion. Corrosive to metals and tissue. Combustion produces toxic oxides of nitrogen.

Air & Water Reactions

Highly flammable. Soluble in water.

Reactivity Profile

Hexamethyleneimine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated in combination with strong reducing agents, such as hydrides.

Hazard

Toxic by ingestion, strong irritant to tissue.

Health Hazard

Inhalation of vapor irritates respiratory tract; high concentrations may cause disturbance of the central nervous system. Ingestion causes burns of mouth and stomach. Contact with concentrated vapor may cause severe eye injury. Contact with liquid causes burns of eyes and skin.

Flammability and Explosibility

Highly flammable

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Purification Methods

Purify azepane by dissolving in Et2O and adding ethanolic HCl until all the base separates as the white hydrochloride, filter, wash with Et2O and dry it (m 236o). The salt is dissolved in the minimum volume of H2O and basified to pH ~ 14 with 10N KOH. The solution is extracted with Et2O, the extract is dried over KOH, evaporated and distilled. The free base is a FLAMMABLE and TOXIC liquid, and best kept as the salt. The nitrate has m 120-123o, the picrate has m 145-147o, and the tosylate has m 76.5o (ligroin). [Müller & Sauerwald Monatsh Chem 48 727 1027, Hjelt & Agback Acta Chem Scand 18 194 1964, Beilstein 20 II 1406, 20 III/IV 1406, 20/4 V 3.]

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