| Identification | More | [Name]
2-Hydroxyethylhydrazine | [CAS]
109-84-2 | [Synonyms]
2-HYDRAZINOETHANOL
2-HYDROXYETHYLHYDRAZINE
BETA-HYDROXYETHYL HYDRAZINE
ETHANOL-2-HYDRAZINE
HYDROXYETHYL HYDRAZINE
1-(2-Hydroxyethyl)hydrazine
2-Hydrazineethanol
2-hydrazino-ethano
2-Hydrazinoethyl alcohol
BOH
Brombloom
Ethanol, 2-hydrazino-
Ethanolhydrazine
HEH
Hydrazineethanol
N-(2-Hydroxyethyl)hydrazine
Omaflora
(2-Hydroxyethyl)drazine
2-Hydroxyethylhydrazine,97%
2-HYDROXYETHYLHYDRAZINE, TECH., 90% | [EINECS(EC#)]
203-711-6 | [Molecular Formula]
C2H8N2O | [MDL Number]
MFCD00007623 | [Molecular Weight]
76.1 | [MOL File]
109-84-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear colorless oily liquid | [Melting point ]
−70 °C(lit.) | [Boiling point ]
155-160 °C32 mm Hg(lit.) | [density ]
1.123 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.493(lit.)
| [Fp ]
165 °F
| [storage temp. ]
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C | [solubility ]
soluble in DMSO, Methanol | [form ]
Liquid | [pka]
14.79±0.10(Predicted) | [color ]
Colorless to Almost colorless | [Water Solubility ]
Soluble in water, alcohols and glycols. | [Merck ]
13,4794 | [BRN ]
1731669 | [InChIKey]
GBHCABUWWQUMAJ-UHFFFAOYSA-N | [Uses]
Intermediate, plant growth regulator, flowering
inducer for pineapples. | [CAS DataBase Reference]
109-84-2(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Hydroxyethylhydrazine(109-84-2) | [EPA Substance Registry System]
109-84-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
R40:Limited evidence of a carcinogenic effect. | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2810 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
KL2800000
| [Hazard Note ]
Toxic | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29280000 |
| Hazard Information | Back Directory | [Hazard]
Moderate fire risk. Irritant. | [Description]
2-Hydroxyethylhydrazine (HEH) is the primary decomposition product of the high-energy ionic liquid 2-hydroxyethylhydrazinium nitrate (HEHN). As a hydrazine fuel, HEHN is the most widely used liquid monocomponent propellant in the aerospace sector. while HEH is a key target for investigating the reaction mechanism of HEHN.
| [Chemical Properties]
Clear colorless oily liquid | [Definition]
ChEBI: 2-hydrazinoethanol is a member of hydrazines. It has a role as a herbicide. It is functionally related to an ethanol. | [Preparation]
2-Hydroxyethylhydrazine is prepared by heating about 2 to 17 parts of hydrazine hydrate dissolved in water to about 30℃ to about 100℃. in a closed system. Then, 1 part of ethylene oxide is gradually added to the hydrazine hydrate, and the temperature of the reaction mixture is maintained in the range of about 30℃ to 70℃ during the addition.
| [General Description]
2-Hydroxyethylhydrazine reacts with β-diketones having strong electron-withdrawing substituents to yield 5-hydroxy-4,5-dihydropyrazoles. | [Biological Activity]
2-Hydroxyethylhydrazine (HEH) is a potent and highly specific inhibitor of the phosphatidylethanolamine methylation pathway in Saccharomyces cerevisiae. Following HEH addition to culture medium, the incorporation of L-[3-14C]serine, L-[methyl-14C]methionine, and S-adenosyl-L-[methyl-14C]methionine into phosphatidylcholine was markedly reduced. In the presence of this inhibitor, cells ceased growth with an IC50 value of 66 pM. Although cellular activity remained unaffected, the addition of choline restored cell growth. This indicates that active phospholipid methylation is unnecessary as long as phosphatidylcholine is supplied via the CDP-choline pathway. The restoration of cell growth by choline suggests that HEH's primary target in vivo is phospholipid methylation. | [Synthesis]
The general procedure for synthesizing 2-hydrazinoethanol from ethylene oxide was as follows: ethylene oxide was added to a VO1 liquefied gas storage tank and pressurized to 1.0~1.5 MPa using nitrogen. 80% hydrazine hydrate was added to a VO2 storage tank, and the molar ratio of hydrazine hydrate to ethylene oxide was controlled to be 8:1. the hydrazine hydrate was fed at a total feed flow rate of 2.0 L/h via feed pumps PO1 and PO2, respectively. The temperature of the micro-mixer was maintained at 40°C, the temperature of the cracking reactor was set at 60°C, the temperature of the micro-heat exchanger was controlled in the range of 0-10°C, and the back pressure of the back-pressure valve was set at 1.5-2.5 MPa. The two liquid feedstocks were mixed in a CPMM-R300 micro-mixer and then entered into the cracking reactor for further reaction. The reaction liquid is cooled by a micro heat exchanger and then micro-fed to the receiving vessel. Most of the water and excess hydrazine hydrate were removed by decompression distillation, and the final colorless oily liquid 2-hydroxyethylhydrazine was obtained. The purity of the product was 89.5% and the yield was 98% by GC. Finally, the entire microreactor system was washed using water. | [References]
[1] Patent: CN104876833, 2016, B. Location in patent: Paragraph 0037; 0038
[2] Patent: EP2952509, 2015, A1. Location in patent: Paragraph 0041; 0042
[3] Bulletin de la Societe Chimique de France, 1939, vol. <5> 6, p. 708,714
[4] Ukrainskii Khimicheskii Zhurnal (Russian Edition), 1928, vol. 3, p. 125,128
[5] Chem. Zentralbl., 1930, vol. 101, # I, p. 2867 |
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