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Chrysanthemic Acid

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Name

Chrysanthemic Acid

EINECS 233-941-2
CAS No. 10453-89-1 Density 1.077g/cm3
PSA 37.30000 LogP 2.30940
Solubility N/A Melting Point 50-51 °C
Formula C10H16 O2 Boiling Point 246.4oC at 760 mmHg
Molecular Weight 168.236 Flash Point 119oC
Transport Information N/A Appearance N/A
Safety A poison by intravenous route. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors. Risk Codes N/A
Molecular Structure Molecular Structure of 10453-89-1 (2,2-DIMETHYL-3-(2-METHYLPROP-1-ENYL)CYCLOPROPANECARBOXYLIC ACID) Hazard Symbols N/A
Synonyms

Chrysanthemummonocarboxylicacid (6CI);Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-(9CI);Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methylpropenyl)- (8CI);2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid;3,3-Dimethyl-2-(2-methyl-1-propenyl)cyclopropanecarboxylic acid;3-Isobutenyl-2,2-dimethylcyclopropanecarboxylic acid;Chrysanthemic acid;Chrysanthemumic acid;NSC 11779;

Article Data 71

Chrysanthemic Acid Synthetic route

5460-63-9

chrysanthemumic acid methyl ester

10453-89-1

chrysanthemumic acid

Conditions
ConditionsYield
With toluene-4-sulfonic acid In water at 110℃; for 6h;99.5%

dibromomethyl chrysanthemate

10453-89-1

chrysanthemumic acid

Conditions
ConditionsYield
With toluene-4-sulfonic acid In water at 120℃; for 10h;99.5%
97-41-6

ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate

10453-89-1

chrysanthemumic acid

Conditions
ConditionsYield
With water; sodium hydroxide In tetrahydrofuran; methanol at 80℃; Inert atmosphere;91%
Stage #1: ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate With sodium hydroxide; water In tetrahydrofuran; methanol at 80℃; for 4h;
Stage #2: With hydrogenchloride In water
90%
Stage #1: ethyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate With sodium hydroxide; water In tetrahydrofuran; methanol at 80℃; for 4h;
Stage #2: With hydrogenchloride In water
90%
alkaline hydrolysis;
With sodium hydroxide In diethyl ether; ethanol; water
5617-92-5

chrysanthemol

10453-89-1

chrysanthemumic acid

Conditions
ConditionsYield
With ruthenium trichloride; potassium hydroxide; potassium peroxomonosulphate for 7h; Ambient temperature;66%
racemic 2,2-dimethyl-3-isobutenyl-cyclopropane carboxylic acid

racemic 2,2-dimethyl-3-isobutenyl-cyclopropane carboxylic acid

31896-10-3, 56287-78-6

N-(2,2,2-trichloro-1-piperazin-1-yl-ethyl)-formamide

10453-89-1

chrysanthemumic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In chloroform; water53.6%
7427-85-2

(2,2-dimethyl-3-(2-methylprop-1-en-1-yl))cyclopropane-1-carbaldehyde

10453-89-1

chrysanthemumic acid

Conditions
ConditionsYield
With sodium hydroxide; silver nitrate In water for 0.5h;48%
(+)-2,2-dimethyl-3-isobutenyl-cyclopropane carboxylic acid [α]

(+)-2,2-dimethyl-3-isobutenyl-cyclopropane carboxylic acid [α]

31896-10-3, 56287-78-6

N-(2,2,2-trichloro-1-piperazin-1-yl-ethyl)-formamide

10453-89-1

chrysanthemumic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In water
10453-89-1

chrysanthemumic acid

Conditions
ConditionsYield
With boron trichloride In toluene

dichloroethyl chrysanthemate

10453-89-1

chrysanthemumic acid

Conditions
ConditionsYield
With toluene-4-sulfonic acid In water at 100℃; for 8h;
83282-91-1

2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl alcohol

10453-89-1

chrysanthemumic acid

A

271241-14-6

2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate

B

n-propyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate

Conditions
ConditionsYield
Stage #1: 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl alcohol With zircornium(IV) n-propoxide In propan-1-ol; xylene at 143 - 145℃;
Stage #2: chrysanthemumic acid With 2,6-di-tert-butyl-4-methyl-phenol In propan-1-ol; xylene at 145 - 147℃; for 8h; Product distribution / selectivity;
A 97%
B n/a

Chrysanthemic Acid Chemical Properties

Chemistry informtion about Chrysanthemic Acid (CAS NO.10453-89-1) is:
IUPAC Name: 2,2-Dimethyl-3-(2-Methylprop-1-Enyl)Cyclopropane-1-Carboxylic Acid
Synonyms: 2,2-Dimethyl-3-(2-Methyl-1-Propenyl)-Cyclopropanecarboxylicaci ; 2,2-Dimethyl-3-(2-Methylpropenyl)-Cyclopropanecarboxylicaci ; Chrysanthemumicacid ; Chrysanthemummonocarboxylicacidmixedisomers ; Chrysanthemum Monocarboxylic Acid ; Chrysanthemic Acid ; Cis/Trans-Chrysanthemic Acid ; 2,2-Dimethyl-3-(2-Methylprop-1-Enyl)Cyclopropanecarboxylic Acid
MF: C10H16O2
MW: 168.23
EINECS: 233-941-2 
Density: 1.077 g/cm3
Flash Point: 119 °C 
Boiling Point: 246.4 °C at 760 mmHg
Vapour Pressure: 0.0088 mmHg at 25°C 
Enthalpy of Vaporization: 53.25 kJ/mol
Following is the molecular structure of Chrysanthemic Acid (CAS NO.10453-89-1) is:

Chrysanthemic Acid Production

Raw materials: isobutylene --> 1-hexene --> isobutyryl chloride --> ethyl chrysanthemumate --> 3-methyl-1-butene --> diazoacetic acid --> estrone(rg) --> 1-heptene --> orthoacetic acid

Chrysanthemic Acid Toxicity Data With Reference

1.    

cyt-mus-ihl 1248 mg/m3

    GISAAA    Gigiena i Sanitariya. 51 (1)(1986),16.
2.    

orl-rat LD50:2500 mg/kg

    GISAAA    Gigiena i Sanitariya. 51 (1)(1986),16.
3.    

ihl-rat LC:>400 mg/m3

    GTPZAB    Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 31 (7)(1987),53.
4.    

orl-mus LD50:1250 mg/kg

    GISAAA    Gigiena i Sanitariya. 51 (1)(1986),16.
5.    

ihl-mus LC:>400 mg/m3

    GTPZAB    Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 31 (7)(1987),53.
6.    

skn-mus LD50:>5 g/kg

    GISAAA    Gigiena i Sanitariya. 51 (1)(1986),16.
7.    

ipr-mus LD50:150 mg/kg

    NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD691-490 .
8.    

ivn-mus LD50:56 mg/kg

    CSLNX*    U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#00083 .
9.    

orl-gpg LD50:2500 mg/kg

    GISAAA    Gigiena i Sanitariya. 51 (1)(1986),16.

Chrysanthemic Acid Consensus Reports

Reported in EPA TSCA Inventory.

Chrysanthemic Acid Safety Profile

A poison by intravenous route. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.

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